Recently, the development of biofuel has been underway in order to cope with the issue of oil depletion and reduce carbon dioxide emissions. One example of a biofuel is biodiesel fuel. Biodiesel fuel containing a hydrocarbon in a certain percentage is expected to be used as an alternative of light oil.
A known example of a method for producing a hydrocarbon is a method comprising reducing an aldehyde using an enzyme or a metal catalyst. For example, Non-Patent Document 1 (Schirmer, Andreas et al., Microbial Biosynthesis of Alkanes, Science, 2010, 329(5991), 559-562) discloses a method for producing a hydrocarbon from an aldehyde using an enzyme, comprising converting acyl-ACP, which is an intermediate of fatty acid synthesis, into an aldehyde with the use of acyl-ACP reductase (AAR) and then converting the aldehyde into a hydrocarbon and CO with the use of aldehyde decarbonylase (AD). In addition, Non-Patent Document 2 (Jingjing Zhang et al., Conversion of fatty aldehydes into alk (a/e)nes by in vitro reconstituted cyanobacterial aldehyde-defortnylating oxygenase with the cognate electron transfer system, Biotech, Biofuels, 2013, 6(86). 1-10) discloses conversion of an aldehyde into a hydrocarbon and formic acid. However, AD has low enzyme activity and is inactivated by H2O2, which is generated by NADPH necessary for reaction. In a method using AD, it is difficult to avoid enzyme deactivation caused by H2O2 generated during reaction, which results in significant reduction in enzyme reaction efficiency. For the above reasons, it is difficult to convert an aldehyde into a hydrocarbon with high efficiency through a method using an enzyme.
In addition, as an example of a method for producing a hydrocarbon from an aldehyde using a metal catalyst, Non-Patent Document 3 (Arian E. Roa et al., Decarbonylation of Aliphatic Aldehydes by a TpMe2Ir (III) Metallacyclopentadiene, Organometallics, 2012, 31, 716-721) discloses a decarbonylation reaction of aliphatic aldehydes by a TpMe2Ir (III) metallacyclopentadiene. Further, Non-Patent Document 4 (Tomohiro Iwai et al., The iridium-catalyzed decarbonylation of aldehydes under mild condition. Chem. Commun., 2008, 6215-6217) discloses a decarbonylation reaction of aldehydes by using an iridium catalyst. Furthermore, Non-Patent Document 5 (Atanu Modak et al., A general and efficient aldehyde decarbonylation reaction by using a palladium catalyst, Chem. Commun., 2012, 48, 4253-4255) discloses a decarbonylation reaction of aldehydes by using a palladium catalyst. However, in the cases of the conventional methods using metal catalysts, a reaction is carried out using an organic solvent at a relatively high temperature. Therefore, it is desirable to safely carry out the reaction under mild conditions.